October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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31Functional Group Exchanges
178, for example, gave 179, and subsequent treatment with potassium tert-butoxide
gave 180 (methyl 4-(N,N-dimethylamino)prop-2-ynoate).
154
H
2
N
CO
2
H
H
2
N
CO
2
H
H
2
N
CO
2
H
SPh
S
O O
Ph
PhSH, Triton B
EtOH, 45°C
6 h
30% H
2
O
2
17 157
61
77
CC
CO
2
H
Me
2
N
Me
2
N
CO
2
Me
Me
2
N
Br
CO
2
Me
178 179 180
40%
Br
2
t-BuOK
Aziridines are formed from 2-amino alcohols, and function as amino acid precur-
sors via formation of an aziridine, using cyanide as a carboxyl surrogate. Reaction
of chiral 2-amino 1-propanol with nosyl chloride (nosyl = nitrobenzenesulfonyl) fol-
lowed by basication led to the N-nosyl aziridine, 181.
155
Subsequent ring opening
with NaCN and hydrolysis ...
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